Microwave‐Assisted Four‐Component, One‐Pot Condensation Reaction: An Efficient Synthesis of Annulated Pyridines.

Yan, Chao‐Guo; Cai, Xi‐Mei; Wang, Qi‐Fang; Wang, Ting‐Yu; Zheng, M.

doi:10.1002/chin.200732148

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“…Prompted by these observations and starting from (Z)-3-benzylidene phthalide, the series of new 1,2,4-trazoles (3a-e), and 1,3,4-oxadiazoles (5a-f) were commonly performed under usual mild and thermal methods, while a simple and efficient one-pot procedure was followed for generation of 1,2,4-triazines (6a-f) with microwave assistance. The use of microwave energy to activated organic reactions has taken a new dimention in the last few years, due to its supreme properties represented by an excellent approach for the safe, rapid, enviromentally safe, inexpensive and yield enhancement (Deka et al, 2001;Chérouvrier and Bazureau, 2001;Xiuying et al, 2003;Yan et al, 2007).…”

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confidence: 99%

The Use of 3-Bezylidene Phthalide as Synthon in Synthesis of Heterocyclic Compounds

Younis¹

2011

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2-(α-Phenylacetyl) benzohydrazide (1) was prepared through the reaction of (Z)-3benzylidene phthalide and hydrazine hydrate. Treatment of compound (1) with substituted benzoyl chloride yielded N'-aroyl-2-(α-phenyl acetyl) benzohydrazide (2a-e) which upon reaction with ammonium acetate provided the corresponding 2-phenyl-1-(2-(5-aryl-1,2,4triazole-3-yl)phenyl)ethanones (3a-e). While the reaction of compound (1) with substituted benzaldehyde gave the hydrazones represented by N'-arylidene-2-(α-phenylacetyl) benzohydrazide derivatives (4a-f). Intramolecule cyclization of the latter compounds by means of acetic anhydride yielded 2-(α-phenylacetyl)phenyl-4-acetyl-4,5-dihydro-5-aryl-1,3,4oxadiazoles (5a-f). Compounds 2-(α-phenylacetyl)-N-(3,6-diphenyl-5-aryl-5,6-dihydro-1,2,4-triazine-4yl) benzamide (6a-f) were also obtained from the direct Diel-Alder reaction between dibenzylidine hydrazine as diene and compounds (4a-f) as dienophile enhanced by microwave irradiation. The assigned structure of the prepared compounds were corroborated by available physical and spectral methods.

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Section: Introductionmentioning

confidence: 99%

The Use of 3-Bezylidene Phthalide as Synthon in Synthesis of Heterocyclic Compounds

Younis¹

2011

RJS

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Microwave‐Assisted Four‐Component, One‐Pot Condensation Reaction: An Efficient Synthesis of Annulated Pyridines.

Abstract: The simple procedure affords polysubstituted and annulated pyridines. Advantages are the short reaction time, simple experimental procedures and product isolation. -(YAN*, C.-G.; CAI, X.-M.; WANG, Q.-F.; WANG, T.-Y.; ZHENG, M.; Org. Biomol. Chem. 5 (2007) 6, 945-951; Coll. Chem.

Cited by 1 publication

References 1 publication

The Use of 3-Bezylidene Phthalide as Synthon in Synthesis of Heterocyclic Compounds

The Use of 3-Bezylidene Phthalide as Synthon in Synthesis of Heterocyclic Compounds

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